TW200418901A - Process for the manufacture of polyester via hydrogenation treatment of recycled diol - Google Patents

Process for the manufacture of polyester via hydrogenation treatment of recycled diol Download PDF

Info

Publication number: TW200418901A
Authority: TW; Taiwan
Prior art keywords: diol; acid; hydrogenated; slurry; group
Prior art date: 2003-02-25

Application number

TW093102400A

Other languages

English (en)

Chinese (zh)

Inventor

Finbar Gerald Mcdonnell

Clive Alexander Hamilton

Alexander Stuart Coote

Original Assignee

Du Pont

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-02-25

Filing date

2004-02-03

Publication date

2004-10-01

2004-02-03 Application filed by Du Pont filed Critical Du Pont

2004-10-01 Publication of TW200418901A publication Critical patent/TW200418901A/zh

Links

150000002009 diols Chemical class 0.000 title claims abstract description 72
229920000728 polyester Polymers 0.000 title claims abstract description 47
238000000034 method Methods 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title claims abstract description 19
238000005984 hydrogenation reaction Methods 0.000 title claims description 26
238000004064 recycling Methods 0.000 claims abstract description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 76
239000003054 catalyst Substances 0.000 claims description 33
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
239000002002 slurry Substances 0.000 claims description 12
-1 propylene glycol butanol monocarboxylic acid Chemical class 0.000 claims description 11
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
238000005809 transesterification reaction Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
239000007789 gas Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
229910052742 iron Inorganic materials 0.000 claims description 5
239000000178 monomer Substances 0.000 claims description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
239000000463 material Substances 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
230000000379 polymerizing effect Effects 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
229910052707 ruthenium Inorganic materials 0.000 claims description 3
229910052732 germanium Inorganic materials 0.000 claims description 2
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
238000011084 recovery Methods 0.000 claims description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
229910052763 palladium Inorganic materials 0.000 claims 2
229910052697 platinum Inorganic materials 0.000 claims 2
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
229910052703 rhodium Inorganic materials 0.000 claims 1
239000010948 rhodium Substances 0.000 claims 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
239000006188 syrup Substances 0.000 claims 1
235000020357 syrup Nutrition 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
239000012535 impurity Substances 0.000 description 15
238000005886 esterification reaction Methods 0.000 description 14
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 12
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 12
229920000642 polymer Polymers 0.000 description 12
230000032050 esterification Effects 0.000 description 11
238000006068 polycondensation reaction Methods 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
239000010936 titanium Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
229910052719 titanium Inorganic materials 0.000 description 6
238000002156 mixing Methods 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000000956 alloy Substances 0.000 description 4
229910045601 alloy Inorganic materials 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
239000011572 manganese Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
229920000139 polyethylene terephthalate Polymers 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000010586 diagram Methods 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
239000005020 polyethylene terephthalate Substances 0.000 description 3
JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical class [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 3
238000010998 test method Methods 0.000 description 3
238000004383 yellowing Methods 0.000 description 3
HXZILEQYFQYQCE-UHFFFAOYSA-N 2-methylcyclopentane-1,3-dione Chemical compound CC1C(=O)CCC1=O HXZILEQYFQYQCE-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
229910052787 antimony Inorganic materials 0.000 description 2
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000835 fiber Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000002861 polymer material Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000005882 aldol condensation reaction Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
238000010292 electrical insulation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000010408 film Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
238000011068 loading method Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229920001707 polybutylene terephthalate Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000013022 venting Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)

TW093102400A 2003-02-25 2004-02-03 Process for the manufacture of polyester via hydrogenation treatment of recycled diol TW200418901A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US44975903P	2003-02-25	2003-02-25

Publications (1)

Publication Number	Publication Date
TW200418901A true TW200418901A (en)	2004-10-01

Family

ID=32927560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW093102400A TW200418901A (en)	2003-02-25	2004-02-03	Process for the manufacture of polyester via hydrogenation treatment of recycled diol

Country Status (16)

Country	Link
EP (1)	EP1599529B1 (ar)
KR (1)	KR20050107449A (ar)
CN (1)	CN100374479C (ar)
AR (1)	AR043260A1 (ar)
AT (1)	ATE446978T1 (ar)
BR (1)	BRPI0407645A (ar)
CA (1)	CA2519335A1 (ar)
DE (1)	DE602004023822D1 (ar)
EG (2)	EG23535A (ar)
ES (1)	ES2335346T3 (ar)
MX (1)	MXPA05008818A (ar)
SA (1)	SA04250080B1 (ar)
TR (1)	TR200503322T2 (ar)
TW (1)	TW200418901A (ar)
WO (1)	WO2004076513A2 (ar)
ZA (1)	ZA200506716B (ar)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI473832B (zh)	2009-03-13	2015-02-21	Saudi Basic Ind Corp	聚對酞酸乙二酯的製造方法
EP2287225A1 (en)	2009-08-20	2011-02-23	Saudi Basic Industries Corporation	Process for making polyethylene terephthalate
KR102306544B1 (ko) *	2017-09-07	2021-09-30	주식회사 엘지화학	에스터화 반응에서의 1가 알코올의 제거 방법 및 이를 포함하는 에스터 조성물의 제조 방법

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE720959A (ar) *	1967-09-18	1969-03-17
JPS511403A (en) *	1974-06-18	1976-01-08	Toyo Boseki	Echirengurikooruno seiseiho
DD247579A3 (de) *	1983-01-10	1987-07-15	Leipzig Chemieanlagen	Verfahren zur herstellung von polybutylenterephthalat
JPH0635404B2 (ja)	1985-02-27	1994-05-11	三菱化成株式会社	粗１，４−ブタンジオ−ルの精製方法
DE3943129A1 (de) *	1989-12-28	1991-07-04	Huels Chemische Werke Ag	Verfahren zur herstellung von thermoplastischen, hochmolekularen copolyestern
JPH0511403A (ja) *	1990-09-18	1993-01-22	Toray Ind Inc	ポルフイン系記録材料
WO2001027849A2 (en) *	1999-10-13	2001-04-19	Troba, Inc.	Electronic shopping management: task models
DE19963442A1 (de) *	1999-12-28	2001-07-05	Basf Ag	Farbzahlverbesserung von mehrwertigen Alkoholen durch Hydrierung
US6380352B1 (en)	2000-08-29	2002-04-30	Eastman Chemical Company	Polyester precursor purification process

2004
- 2004-02-03 TW TW093102400A patent/TW200418901A/zh unknown
- 2004-02-23 EG EG2004020077A patent/EG23535A/xx active
- 2004-02-23 AR ARP040100558A patent/AR043260A1/es unknown
- 2004-02-24 CA CA002519335A patent/CA2519335A1/en not_active Abandoned
- 2004-02-24 CN CNB2004800049845A patent/CN100374479C/zh not_active Expired - Fee Related
- 2004-02-24 EP EP04714233A patent/EP1599529B1/en not_active Expired - Lifetime
- 2004-02-24 ES ES04714233T patent/ES2335346T3/es not_active Expired - Lifetime
- 2004-02-24 WO PCT/US2004/005920 patent/WO2004076513A2/en not_active Ceased
- 2004-02-24 KR KR1020057015570A patent/KR20050107449A/ko not_active Ceased
- 2004-02-24 ZA ZA200506716A patent/ZA200506716B/xx unknown
- 2004-02-24 TR TR2005/03322T patent/TR200503322T2/xx unknown
- 2004-02-24 BR BRPI0407645-1A patent/BRPI0407645A/pt not_active IP Right Cessation
- 2004-02-24 MX MXPA05008818A patent/MXPA05008818A/es unknown
- 2004-02-24 AT AT04714233T patent/ATE446978T1/de not_active IP Right Cessation
- 2004-02-24 DE DE602004023822T patent/DE602004023822D1/de not_active Expired - Lifetime
- 2004-04-18 SA SA4250080A patent/SA04250080B1/ar unknown
2005
- 2005-08-24 EG EGNA2005000495 patent/EG23887A/xx active

Also Published As

Publication number	Publication date
TR200503322T2 (tr)	2005-10-21
KR20050107449A (ko)	2005-11-11
DE602004023822D1 (de)	2009-12-10
BRPI0407645A (pt)	2006-02-21
ATE446978T1 (de)	2009-11-15
CN100374479C (zh)	2008-03-12
EG23887A (en)	2007-12-12
AR043260A1 (es)	2005-07-20
WO2004076513A2 (en)	2004-09-10
CA2519335A1 (en)	2004-09-10
ES2335346T3 (es)	2010-03-25
MXPA05008818A (es)	2005-10-18
EP1599529A2 (en)	2005-11-30
ZA200506716B (en)	2007-03-28
CN1784448A (zh)	2006-06-07
EP1599529B1 (en)	2009-10-28
SA04250080B1 (ar)	2008-05-04
WO2004076513A3 (en)	2004-12-16
EG23535A (en)	2006-04-19

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